Tripadvisor, Airbnb: Can AI Agents Beat Travel Agents?

For many people, planning and booking a holiday includes a shop, a uniformed travel agent and wall-to-wall glossy brochures.

These things are still a thing, but the thirst for cheaper and faster everything is driving all industries to drink from the well of AI.

Travel & Tourism is no exception, with the industry undergoing a dramatic conversion from the traditional human travel agent to the sophisticated AI agent.

The change is replacing rigid search filters with fluid, natural language conversations that enable customers to plan a full holiday itinerary in minutes.

Leading this planning revolution are five global giants: Booking Holdings, Expedia Group, Airbnb, Tripadvisor and Marriott International.

The businesses are creating "conversational concierges" that understand personal nuances and "vibe-based" requests.

By integrating Large Language Models (LLMs) with proprietary data, they are seeking to make trip discovery as personalised as a bespoke human consultation.

Connected trip vision expands

Booking Holdings is at the forefront of this evolution, using AI to recreate the intimacy of human service.

Glenn Fogel, CEO, believes that artificial intelligence is poised to bring back the kind of personalised service travellers once got from a human agent, through the devices they use every day.

Through tools like its AI Trip Planner and Penny, the group creates bookable, curated itineraries that actively manage the full travel experience.

Glenn says: “We're advancing our connected trip vision and continuing to build out AI capabilities that create more value for travellers and partners.”

The technology also manages real-time disruptions, such as reworking plans due to weather or missed reservations.

Internal superpowers drive efficiency

Glenn accepts that there are huge challenges to face saying: “It’s the dawn of a new age and the problem is nobody has a good sense of what the future’s going to be.”

Expedia Group is also "experimenting aggressively" with its intelligent sidekick, Romie.

This assistant lives in messaging threads to help groups agree on villas and track flight prices.

Ariane Gorin, Expedia Group CEO, explains that AI opens new growth opportunities: “We’re working with all the major platforms, ensuring our brands show up prominently in gen AI searches and function effectively with agentic browsers.”

Internally, the company uses technology to transform operations and efficiency. Ariane says: “We’re deploying AI internally to give our teams superpowers. Our product and tech teams are using AI to design and build products.”

Personalised native experiences evolve

Ariane also sees potential in using technology to make advertising more effective and improving recommendations through natural language engagement.

At Airbnb, the strategy is to move beyond the traditional search bar. Brian Chesky, Airbnb CEO, is positioning the brand for a deeply personalised agentic experience, where the technology understands the user.

The company’s Project Y uses LLMs to aid discovery and help hosts manage properties more effectively. Brian explains: “We are building an AI-native experience where the app does not just search for you. It knows you.

“It will help guests plan their entire trip, help hosts better run their businesses and help the company operate more efficiently at scale.” Airbnb is currently testing features allowing users to ask questions about locations using natural language.

Proprietary data creates magic

Technology also enhances safety at Airbnb by verifying the identities of 200 million users and automating 33% of customer support. Similarly, Tripadvisor is leaning on its database of one billion reviews to provide "magic" through its AI Trip Builder.

Matt Goldberg, Tripadvisor CEO, says that trust is the most precious commodity in this new world: "In a world of AI, trust becomes increasingly more rare, more precious and more valuable – knowing who you can trust and the provenance of where that information came from."

By grounding GPT-4 in proprietary first-party data, the platform avoids generic results. Rahul Todkar, Tripadvisor’s Head of Data and AI, likens the marriage of rich content and personal preferences to "magic", aiming for highly personalised planning.

Redefining customer acquisition

Rahul says: "The goal is to make trip planning highly personalised by combining all the Tripadvisor content with OpenAI's advanced AI capabilities."

Marriott International is using technology to redefine the area of customer acquisition. Through the Bonvoy AI Assistant, the hotel giant offers "Lux-scaping". Offering premium additions based on loyalty profiles and historical spending habits.

Anthony Capuano, Marriott International CEO, sees this as a significant change in how hotels find and keep guests. Anthony says: “We see AI as an opportunity to potentially redefine the customer acquisition paradigm that has governed our industry for the past several decades.”

Marriott plans to deploy natural language search in early 2026. Anthony says: “We're pulling into the players' parking lot. We're not even in uniform on the field.”

How the travel titans are using AI

Booking Holdings

• Integrating AI across its business to deliver a "Connected Trip" experience
• AI Trip Planner and Penny on Priceline function as conversational concierges
• Travellers can describe specific needs – such as a romantic pet-friendly weekend – and receive an instantly bookable itinerary
• The company uses AI to manage disruptions like weather-related changes and missed reservations
• The integration of generative AI into customer service has produced lower cancellation rates and better customer conversion.

Expedia Group

• Consolidated its technology stack to power Romie, an AI "travel sidekick" that operates within SMS and WhatsApp threads
• Romie helps with group planning, tracks flight prices in real-time and proactively suggests alternatives during weather disruptions
• CEO Ariane Gorin is focused on "agentic browsers" and ensuring the brand appears prominently in AI-driven searches
• The company is experimenting with integrations across major platforms like ChatGPT and Google to better target and convert travellers.

Airbnb

• Moving from a traditional search to an AI-native platform through its "Project Y" and conversational search initiatives
• CEO Brian Chesky wants the app to "know" the user rather than just searching for them
• It will use large language models to understand "vibe-based" requests, such as searching for a "quiet cabin with a fast kitchen" instead of just a city location
• The AI-native experience is designed to help guests plan entire trips and assist hosts in running their businesses more efficiently
• Airbnb uses AI to enhance platform safety by verifying the identities of 200 million users.

Tripadvisor

• Its AI Trip Builder combines OpenAI’s GPT-4 engine with the "fuel" of one billion proprietary user reviews
• The system connects clickstream, transactional and user information behind a proprietary firewall to offer highly personalised recommendations
• It has expanded its reach through partnerships with Perplexity AI and a dedicated app in the ChatGPT Store
• For the 2026 FIFA World Cup, the platform has launched a specific 'Go for the Goal' planner to help fans navigate complex multi-city trips.

Marriott International

• Transformed its Bonvoy app into a full-service AI travel consultant
• The Bonvoy AI Assistant uses traveller loyalty profiles, including room preferences and dining habits, to suggest destinations and hotels
• A key innovation is "Lux-scaping," where the AI suggests luxury additions, such as a spa day, based on historical spending
• Marriott is deploying natural language search on its website and app in the first half of 2026 and has entered strategic partnerships with Google and OpenAI.